Facile enantioselective ring-opening reaction of meso epoxides with anilines using (S)-(-)-BINOL-Ti complex as a catalyst

The catalytic enantioselective ring-opening reaction of mesostilbene oxide and cyclohexene oxide with anilines was catalyzed by (S)-(-)-BINOL-Ti complexes at ambient temperature to obtain beta-amino alcohols in high yield (95 %) and enantioselectivity lee, 78 %). The enantiemeric excess (ee) of the product was further improved to 98 % by a single recrystallization step. The absolute configuration of representative beta-amino alcohols was determined by single-crystal X-ray diffraction analysis. The catalyst recovered after first use was recycled four times with retention in its performance. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).